


Dressing Up

by Lonewritersclub



Series: There Were Three of Them [3]
Category: Pirates of the Caribbean (Movies)
Genre: Black Pearl - Freeform, Clothing Kink, F/M, Feminization, Gen, Genderplay, M/M, Pirates, corsets
Language: English
Status: Completed
Published: 2020-12-23
Updated: 2020-12-23
Packaged: 2021-03-11 02:07:04
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,545
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28267350
Author URL: https://archiveofourown.org/users/Lonewritersclub/pseuds/Lonewritersclub
Summary: Elizabeth needs Jack to pose as a princess kidnapped by the captain of the Black Pearl to attain her father's sword from the general. They have the dress, the corset and everything necessary but will Jack play along? Will is there to help Jack dress up and Barbossa, well, he is there to mainly enjoy the process.Excerpt:“Hush now, Jack. You should already be used to this.” Jack huffed out immediately at Will’s comment in utter incredulousness but Will wasn’t agreeing with him even if he only did so to hope to comfort Jack along with the intimate touch of his hands on his shapely body. “You know, that ever-prevalent scarf you wear around your waist with a dozen belts looped around it? It is much like this corset”, Will added and then traced his large, rough hands from Jack’s flat bosom to the smallest point of his waist. He could nearly close his hands around it entirely. Jack shivered in Will’s cherishing hold, leaning his head towards Will’s shoulder behind him.
Relationships: Elizabeth Swann/Will Turner, Jack Sparrow/Elizabeth Swann, Jack Sparrow/Elizabeth Swann/Will Turner, Jack Sparrow/Will Turner
Series: There Were Three of Them [3]
Series URL: https://archiveofourown.org/series/2070825
Comments: 2
Kudos: 58





	Dressing Up

**Author's Note:**

> Anyone else have this weird false memory of Sparrow wearing a dress in one of the movies? Or is it just me? Because apparently he did not in actuality.

Somewhere in the middle of the Mexican Gulf, a ship with dark sails hummed in the cool winter night. It was quiet and serene outside on the deck with a man without a tongue expertly looking after the helm. Inside the captain’s quarters however there was an argument to be had with the head of management of the Black Pearl.

“I truly do not see, this curious submission proposed by the lot of you, of how _I’m_ supposed to be the most suitable candidate to be impersonating the captive princess when I can state with a considerable amount of confidence that we can all distinctly see that here we have an actual woman, and a something such as true royalty already herself, among us right at this current moment”, the captain feistily complained. He was standing behind a crimson Chinese screen they had purchased during their latest trip to Singapore and groaning. His usual items of clothing were thrown over the screen with his effects and it was all referring to his indisputable nudity beyond the thin partition. But he wasn’t alone – Will was behind the screen with him helping him put his novel attire on although not to the captain’s delight.

Elizabeth lounged on the grand bed opposite to the changing quarters and shot it a stern look.

“Jack, you are fully aware that I cannot wear a corset like that to save my life, but rather in fact, end it. Moreover, my face is too familiar to the British navy. But if the infamous captain Sparrow holding the implied princess hostage were the princess himself, nobody would expect it and think she was you. Thus, it’d really be best if you did it.”

“Ms Swann be right”, agreed Barbossa in his raspy voice where he was sitting beside Elizabeth in a plush armchair collected from some ship of French aristocrats. “In addition, you are the only one that can be trusted besides us four to conduct the deed. We are not employing Ragetti and Pintel to pose as fair ladies again, that is for sure. Those two knucleheads couldn’t pretend to be even dirty wash buckets if they were turned into water by a wicked witch.”

“Maybe into two bottles of rum, then?” Jack quipped from behind the screen humorously. “I could use some right about now.”

“This not be about rum right now, Jack. Try to keep your head straight for a second here, would you? How’s the dress coming along?” Barbossa asked leaning slightly to the right to catch a glimpse behind the screen. He just caught the sight of Will then yanking his elbows well pasts his sides, cearly pulling on something forcefully.

“Almost done here”, Will replied through gritted teeth. The answer was followed by a pained yelp.

“Not so tight, you degenerate blacksmith son of a filthy pirate!” Jack panted thinly and moaned in anguish, gripping on his constrained waist. The corset was a simple but an effective one made of quality black silk with whale boning to hold its form, and silk straps at the back. At the chest it came up to Jack’s armpits covering his torso fairly well although underneath it he was naturally wearing a thin black night gown so that the corset wouldn’t rub on him and so that his lower-half wouldn’t be indecently exposed. To Jack’s dismay, though, the gown only came to his half-thigh barely covering his behind properly. At least the matching stockings which had frilly lacing at the tops and went just past his knees gave him some more coverage to his legs. But it still wasn’t enough to make Jack feel at home in these restrictive and tight garments.

“Hush now, Jack. You should already be used to this.” Jack huffed out immediately at Will’s comment in utter incredulousness but Will wasn’t agreeing with him even if he only did so to hope to comfort Jack along with the intimate touch of his hands on his shapely body. “You know, that ever-prevalent scarf you wear around your waist with a dozen belts looped around it? It is much like this corset”, Will added and then traced his large, rough hands from Jack’s flat bosom to the smallest point of his waist. He could nearly close his hands around it entirely. Jack shivered in Will’s cherishing hold, leaning his head towards Will’s shoulder behind him. 

“Only this one _truly_ gives you that minute waist that is so fashionable among the women these days. They would turn green with envy if they ever saw you strut down the streets of London wearing this. And the men would have to cover their laps to save their dignity.”

Will’s sultry low voice his ear and the words he spoke privately only to him distracted Jack for a second from his original ideas but when Barbossa suddenly started coughing behind the screen, he snapped back into reality.

“Thank yee, William”, Jack began and released himself from Will’s grip, “but the shape of my waist is the least of my concerns at the moment. If I am to do this, this crazy plan you concocted up with something aking to the logic I thought only I could hold in my brain, what is it do you propose I do with me upper half then. And I’m talking about my head, not the state of my bust. I’m fairly certain nothing can be put inside this corset unless you’ll have me positively die out of asphyxiation.”

Elizabeth sprang up from the bed and ventured to go behind the screen now too. “Wait, you’re only done with the corset? Let me come see, you clearly have no idea what you’re doing over there, and it’s nearly midnight, I’d like to go to sleep some point tonight as well.”

“No! Absolutely no! I cannot have the opposite sex see me like this, just in these dainty undergarments, as it is. You’d never see me for who I really am after this, Lizzie.”

Elizabeth just laughed away.

“Oh Jack, I’ve always thought you’d make a pretty girl. There’s nothing to be ashamed of, let Barbossa see too. We all need to make sure you’ll look appropriate enough to pass for a princess. Your disguise must not go sideways, at least not before you get the sword from the general’s chambers to us. Then you can flash him all you want”, she responded as if what she was saying was of any relief to Jack. Barbossa chuckled quietly as he imagined the look on Jack’s face at her words.

Will stepped from behind the screen first and was then slowly followed by a reluctant Jack who had his head lowered towards the swaying ground. The dark purple women’s heels that were already on his feet clipped on the hard wood with his self-pitying steps.

Barbossa laughed harder now until that his chest started to ache. Jack’s head snapped up then only to shoot his first mate with a fiery dark gaze. Barbossa ceased his laughing but only to grin right back at him with full confidence. After all, he wasn’t the embarrassed man wearing women’s clothing – even Elizabeth was dressed in a pair of trousers. However, it wasn’t as if Jack appeared embarrassing in wearing just the revealing women’s underclothes and such suggestive ones too – quite the opposite in fact. It looked like they were made for him, or the other way around.

Hector took a relishing bite out of the green apple he had been only playing catch with until then, and kept his eyes locked on the sight of his captain. Jack narrowed his eyes further at him. Will shortly put a steadying hand on the small of Jack’s back in a valiant effort to calm him down.

“You really ought to mind the next words you’ll say to me, Hector. After all, I’m still on the fence about this whole ordeal and I wouldn’t mind you trying on the dress too to play the part – just in case purple happened to be your colour”, Jack told him with a bite to his voice. Barbossa raised his hands up with a softer smile ready to settle back down. He wanted to finish his apple in peace.

Elizabeth wasn’t paying much attention to the exchange between the first mate and the captain at all. Instead she came closer to Jack now that he wasn’t hiding his form so much, and inspected the lace work Will had done on the corset. Will waited for her sign of approval

“It is tight, but not horribly so”, Elizabeth investigated as her fingers ghosted over the black silk lacing behind Jack’s back to the pretty little bow at the end right above Jack’s behind. She turned to face Will with a proud smile. “Well done!” Will smiled back at her warmly gazing into her hazel eyes with deep affection, as per usual. Jack sighed out and rested his hands on his hips with exasperation when they dragged their lovesick moment for long enough.

Elizabeth returned the snort by poking Jack’s restricted chest that could barely move in time with his breaths with her finger. “Not so fun, is it, Jack?” she asked him with a self-satisfied look. “But then again, this could now be my opportunity to rescue you from a corset this time around. To repay your kindness, so to speak”, she added. Jack grinned at her but not nicely.

Barbossa cut in this time. “I reckon the dress can be fitted on now, don’t you think? As much as I can always appreciate the sight of lingerie on a warm body, I do prefer to see a job well done in a timely fashion.”

Elizabeth rolled her eyes but then went and grabbed the dark purple satin gown off the dresser, opened it up and then set it on the floor so that Jack could gingerly step inside it in his heels. Jack slid himself inside the smooth, rich yet cool fabric with the help of both Will and Elizabeth.

“The corset and the dress don’t really match but the general will never see it”, Elizabeth fretted slightly as she did the clasps on the dress on its right side while Will handled the left. When nothing more was said, she glanced at Jack quickly but sternly. “He won’t, right Jack?”

Jack met her gaze with wide innocent eyes. “I sure hope not but you never know what needs to be done in order to complete the mission successfully”, he said back. “And you want me to get you the artefact, don’t you? That’s why you’re making me do all of this in the first place?”

Elizabeth didn’t say a thing, only jerked her arms back as she tightened the dress closed. Jack gasped again from the snug fit across his chest, gripping on Will’s shoulder for dear life.

“It was my father’s sword. He loved it, he never left anywhere without it. He bought it from the same shop Will used to work at”, Elizabeth said glancing at Will with a deep sadness, “It’s the only thing I can hope to have of his at this point. Something to remember him by”, she continued pleading the captain. “Please, Jack. The general has always had a strange infatuation for saving noble damsels in distress. Even unheard of princesses. It probably earns him some respect among his peers in London. This is the best plan to get the general and thereby the sword to us. Could you please do this for me?”

The look in Jack’s eyes softened at Elizabeth’s emotional reasoning and he found himself nodding along slightly.

“As you wish, Lizzie”, Jack reconciled with a small smile to her and smoothed out the front of the dress absentmindedly and was surprised by how lovely it really was. Maybe he could stand wearing it and even the corset for a day. It also gave him some nice back-support. And credited Will’s sultry gaze.

Elizabeth smiled wide and clasped her hands together in front herself happily.

“Brilliant, thank you!” she exclaimed. She pressed a quick smooth on Jack’s cheek but then pulled away with a sudden air to the movement. “Oh, we mustn’t forget. As for your hair and face, the beard really ought to go.”

Jack made an incredulously distressed face at that as he realized the matter as well. It had taken such a long time for him to gather enough beard to braid it in its current state. Elizabeth sympathised with him. “I’m sorry. But as for your hair, we could hide it with a long enough brown wig. We have wigs too, right?”

Will rummaged through the chest they had stolen from their last lift which was full of fair garments and accessories of a noble woman, as was the purple dress. The woman in question however hadn’t been aboard at the time of the bootlegging mission so it was impossible to know to whom they originally belonged to. But rich she admittedly must have been – or rather her husband or family most likely.

Will surprisingly managed to find the most suitable dark brown long wig for Jack from the heavy chest. It was styled in intricate curls and was adorned by golden cast pearls and twinkling little diamonds. A wig of a noble woman indeed.

“While you’re at it, Turner, might you find any white powder in there? Princesses aren’t often this tan even after being kidnapped by a bunch a pirates”, Barbossa asked and Will fetched them a golden compact he assumed contained the stuff.

Jack unravelled his bandana and allowed his forehead to see the light of the quarters for the first time in a long while. Barbossa was surprised to see that Jack wasn’t in fact hiding any hideous scarring or a birth mark underneath it for how much he wore it but it was a forehead like any other. Somehow even the same shade as the rest of his face which Barbossa found utterly confusing. He must secretly sometimes sit in the sun without the scarf on, Barbossa concluded to himself.

Elizabeth took care of placing the wig on Jack’s head and ended up opening up the bun it was tied up in and loosen the curls down to hide Jack’s natural hair underneath it and also match them together in case some locks came to view slightly.

In front of the small mirror set over a bowl of water in the bath nook, Jack shaved his beard with great sorrow. Each glide of the shaving knife made him feel like he was going back in time, making him look years younger. When he was finished, the face in the mirror barely looked recognizable to him, especially with the wig on now too. The shiny, neat waves of the brown wig curled around his smooth face delicately and the pearls glittered prettily in the candle light, and he grimaced to himself. He was starting to look like a woman too easily. It is for Elizabeth, he reminded himself. And Will had a definite heady presence about it whenever Jack noticed to look at him properly. This might not end up being a one-time thing after all…

“Alright, now sit on the bed and I’ll do your make-up”, Elizabeth said with a little too much excitement not to conclude that she wasn’t enjoying this just for the purpose of retrieving her father’s sword using a ludicrous plan.

Jack was too tired at this point to argue but instead of sitting on the bed, he sat himself in Barbossa’s unexpecting lap just to spite him. Hector was about to throw him off but Elizabeth was already on Jack with the powder brush and with her he knew better than to dispute with. She worked on Jack's skin and cleaned up the kohl around Jack’s eyes. A little rouge to his cheeks and lips and Elizabeth finally leaned off to look at the full picture.

“Well?” Jack asked with a raised brow. Will was standing behind her with glaced over look and a tight trousers but Jack wasn’t going to point it out right now. He was sitting in Hector’s lap and even he was beginning to feel like a lumpy seat. Jack decided to stand up.

Elizabeth inspected him quietly and then noticed Jack’s hands – and arms. The tattoos and scars shined off of him with great inconsistency. She hurried over to the chest again and started digging through it. After a few moments there was an “aha!”

Jack regarded her suspiciously as she returned to him with a pair of white satin gloves. They went up to the half point of his bicep, effectively covering his tattoos. There was barely a sliver of the skin on his arms showing between the gloves and the gown's frilly sleeve.

“They don’t match the colour so well but they were the longest ones I could find.”

“Great”, Jack just commented and smiled to her hoping everything was finally finished. Then a look of realizing something terrible flashed on her face once again.

“Oh dear”, she muttered quietly.

“What?” Jack was worried now too but more of himself for looking ill or such. As if another nose had grown on him or something of the like, such a horrific event her expression was enough to convey.

Then she answered.

“Your teeth. You have gold teeth.”

Barbossa rumbled with laugher behind Jack. But Elizabeth wasn’t laughing. Not one bit. There was no way they could change his teeth but he couldn’t play a mute either. Could he? Maybe he could pretend he had been so terrified of the capture that he was having trouble speaking. He could be in a shock so to say. And by _he,_ Elizabeth meant the princess. But he would still need to speak if need be. Or scream at appropriate times.

“How about a lovely looking fan?” Will suddenly quipped from behind them. There he was, by the chest, waving a white fan, that had elaborate lacing with gold details at the brim, at himself with a hip jutted out. It made quite the comedic sight. But the fan was actually quite effective in helping him to cool down. The sight of Jack in those pretty fabrics was doing things to him and to his affection for both the ladies as well as certain gents.

“Jack could just cover his mouth with this as he speaks and otherwise remain silent and keep his lips closed. What do you say?”

Elizabeth was utterly delighted. “Oh Will, that’s perfect! Now everything is ready to go once we spread a rumour that the Pearl has captured a princess for ransom.”

Jack took the fan from Will and wondered about it thoughtfully. At the other end of the quarters, there was a heavy full-body length mirror supported by decorative frames against the hull. He slowly walked himself, mindfully in his higher heels, to it. Now that the transformation was complete, Jack took in for the first time his new appearance. Everyone waited quietly for his reaction.

The dark purple colour of the dress that reflected the candlelight in a glowing way suited his dark skin surprisingly well as didn’t offer a harsh contrast which might gain attention to his tanned tone that was mostly unheard of among the noble women, even with the light powder dusted all over the showing skin. But suppose the powder along with the other make-up helped him to simply exude femininity. His eyes were dark but clean and defined. Not half-bad. The wig too was actually quite pretty. Jack wondered, if he should ever let his own hair out from the locks and brushed through them until they would shine like a smooth sea shell in the water, would they be able to look as nice as the wig did. Probably not but it was a tantalizing thought nonetheless.

And Will was quite right about his waist. Looking at himself in the mirror, Jack wondered how he was still breathing. But thankfully Will hadn’t tight-laced him so hard around his chest but rather only at his waist to give him so curve to his body.

The gloves made Jack look quite eloquent and modest, they matched the fan at least. And when Jack raised the fan up to cover just below his eyes, he could not recognize himself barely at all. He looked like a _he_ no more. Not one bit.

He was a princess now.

But where was the _sparkle_?

“Give me some rings over here, would you. There’s barely any diamonds here to catch one’s eyes on for later thieving. I’m a princess after all for goodness sake, I should be dripping with jewellery. There must be some necklaces in that chest too”, Jack ordered the stunned looking lass and the lad while he examined himself in the mirror some more keeping his chin high, twirling the glowing dress around, fanning himself gently or fine-tuning his curls with a fair gloved hand. The startled two quickly went back to the chest once more to find what Jack demanded.

If they wanted him to play a princess, he would give them a damn princess.

Barbossa laughed in his chair some more.

**Author's Note:**

> I made a valiant effort here to get this published today so that it serve here as a Christmas present to any POTC fans. So I hope you liked this even though I didn't get around proof-reading it in advance. Happy holidays! Keep safe!


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